[NH2:1][C:2]1[C:3]([OH:9])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.C(N(CC)CC)C.[F:17][C:18]([F:29])([F:28])[C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(OCC)(=O)C.CO>[Br:8][C:6]1[CH:7]=[C:2]([NH:1][C:23](=[O:24])[C:22]2[CH:26]=[CH:27][C:19]([C:18]([F:17])([F:28])[F:29])=[CH:20][CH:21]=2)[C:3]([OH:9])=[N:4][CH:5]=1
To a solution of 3-amino-5-bromopyridin-2-ol from Step C (1.5 g, 7.9 mol) and triethylamine (1.64 mL, 11.9 mol) in tetrahydrofuran (15.8 mL) at 0 C was added dropwise 4-trifluoromethylbenzoyl chloride (1.2 mL, 7.9 mol). The reaction mixture was stirred at 0° C. for 1 h and warmed to room temperature for 15 h. Potassium carbonate (1.64 g, 11.9 mol) and methanol (15.8 mL) were added and the reaction mixture was stirred at room temperature for 6 h. The reaction mixture was diluted with ethyl acetate (100 mL) and washed with saturated ammonium chloride solution and brine. The separated organic layer was dried with sodium sulfate, filtered and concentrated in vacuo. Purification by medium pressure liquid chromatography on silica gel (1:5 ethyl acetate/hexanes) gave 1.72 g (60%) of the title compound.
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